CN101526737B - Immersion lithography compositions and immersion lithography method - Google Patents

Immersion lithography compositions and immersion lithography method Download PDF

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CN101526737B
CN101526737B CN200810176143.2A CN200810176143A CN101526737B CN 101526737 B CN101526737 B CN 101526737B CN 200810176143 A CN200810176143 A CN 200810176143A CN 101526737 B CN101526737 B CN 101526737B
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following structure
intermediate materials
photoresist
following
photoetching compositions
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CN101526737A (en
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D·王
C·-B·徐
G·G·巴克雷
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Rohm and Haas Electronic Materials LLC
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
    • H01L21/0274—Photolithographic processes

Abstract

The present invention provides a new photoresist composition. The new photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprises two or more distinct materials that can be substantially non-mixable with a resin component of the resist. Particularly preferred photoresists of the invention can exhibit reduced leaching of resist materials into an immersion fluid contacting the resist layer during immersion lithography processing.

Description

Composition and immersion lithography method for immersion lithography
Technical field
The present invention relates to be specially adapted to the novel photoetching compositions of immersion lithography method.The preferred photoetching compositions of the present invention comprises the material that two or more can not mix with the resin Composition of photoresist substantially.The particularly preferred photoresist of the present invention can show in immersion lithography process that low photoresist material leaches into the amount in the immersion liquid contacting with photoresist layer.
Background technology
Photoresist be for by image transfer to the photosensitive film on base material.On base material, form the coating of photoresist, then photoresist layer by photomask exposure in the light source of activating radiation.Photomask has to the opaque region of activating radiation with to other transparent region of activating radiation.Activating radiation exposure makes photoresist coating produce photoinduced chemical transformation, therefore by the design transfer of photomask to applying on the base material of photoresist.After exposure, photoresist is developed, obtain carrying out to base material the camegraph of selectivity processing.
The growth of semi-conductor industry meets More's law, and this law claims that the complicacy of IC equipment on average every two years doubles.This requires to shift and have still less pattern and the structure of characteristic dimension with planography way.
Obtaining more a kind of approach of small-feature-size is to use the light of shorter wavelength, yet, it is difficult that searching shows transparent material to the light lower than 193nm, therefore by using simply a kind of liquid that more light is focused on film, developed the method that improves lens numerical aperture by immersion lithography method.Immersion lithography method for example, is used the fluid of high index between the outermost surface of imaging device (, KrF or ArF ledex) and the first surface of silicon wafer or other base material.
People have carried out some effort to overcome the problem relevant with immersion lithography art.Referring to U.S. Patent application publication 2006/0246373.Immersion lithography use other reliably and easily photoresist and formation method are obviously needed.
Therefore need to be applicable to flood photolithographic new material and method.
Summary of the invention
We are provided for flooding photolithographic new compositions and method now.
The preferred photoresist of the present invention can comprise:
(i) one or more resins,
(ii) can suitably comprise the photoactive component of one or more photic acid producing agents (photoacid generator) compound, and
(iii) two or more different materials, they substantially can not with described one or more mixed with resin.
Accompanying drawing summary
Fig. 1 has described the better photoetching compositions layer of the present invention.
In these photoetching compositions, preferably chemistry strengthens positive interaction photoresist (chemically-amplified positive-acting resist), for example, described resin Composition comprises one or more resins, described resin comprises photic acid labile group, for example photic acid labile ester or acetal (acetal) group.
Substantially the immiscible component of described photoetching compositions suitably comprises at least two kinds of different materials.These different materials sometimes refer to " top material (top material) " and " intermediate materials (intermediate material) " in this article.Preferred top material and intermediate materials are polymkeric substance (resins), and in described polymkeric substance (resin), at least one polymer repeat unit is suitably different.
In good system, described top material and intermediate materials also can be distinguished by hydrophobicity, when particularly the hydrophobicity of described top material is higher than described intermediate materials.Therefore, for example described intermediate materials can comprise more polar group (with respect to described top material), wherein this polar group can suitably comprise one or more heteroatomss (O, N, S), if hydroxyl, halohydrin are (as-CH (OH) (CF 3) 2), carboxyl (COOH), (C (=O) OR, wherein R is C to ester 1-20alkyl), sulfo group (SO 3h) and ether.For example, described top material and intermediate materials are identical general resins (general resin), and a repetitive of different is intermediate materials can comprise halohydrin (for example-CH (OH) (CF 3) 2) substituting group, and the corresponding units of top material is not containing this halohydrin substituting group.
In other good system, the hydrophobicity of described intermediate materials also can be different from the resin Composition of described photoetching compositions, when particularly the hydrophobicity of intermediate materials is higher than resin Composition (similarly, at chemistry, strengthen in positive interaction photoresist, described resin Composition comprises that one or more have the resin of photic acid labile group).Therefore, for example, described one or more resins can comprise more polar group (relatively described intermediate materials and top material), for example (it can suitably comprise one or more heteroatomss (O, N, S), if hydroxyl, halohydrin are (as-CH (OH) (CF for ester or acetal group (it can be photoactive) or other polar group 3) 2), carboxyl (COOH), sulfo group (SO 3h) and ether).
In this good photoresist system, except hydrophobicity difference, the surface of described top material can better be greater than the surface energy of described intermediate materials.In addition, the surface that is preferably described intermediate materials can be greater than the surface energy of described resin Composition (similarly,, in chemistry enhancing positive interaction photoresist, described resin Composition comprises that one or more have the resin of photic acid labile group).For example, the difference of the energy of the surface between described top material and intermediate materials can be at least about 5,10,15,20 or 25 dynes per centimeter.Similarly, the difference of the energy of the surface between described intermediate materials and resin Composition can be at least about 5,10,15,20 or 25 dynes per centimeter.
In this good system, by the difference between hydrophobicity and surperficial energy, the spin-coated layer of described photoetching compositions can have hierarchy construction (graded configuration), the major part of wherein said resin Composition (substantial portion) (similarly, at chemistry, strengthen in positive interaction photoresist, described resin Composition comprises that one or more have the resin of photic acid labile group) can be with respect to described intermediate materials and the more approaching substrate surface below of top material, and the more approaching substrate surface below of top material in the comparable described photoetching compositions layer of the major part of described intermediate materials.Herein, " major part " of top material, intermediate materials or resin Composition represents at least 30,40,50,60 or 70 % by weight of described material or component, in the described material in described photoetching compositions or the general assembly (TW) of component.
In step of exposure, in the process contacting with immersion liquid, particularly preferred photoresist of the present invention can show that low photoresist component is to the amount of immersion liquid migration (leaching).Importantly, without applying the overlayer of any type or apply barrier layer on photoresist between photoresist layer and immersion liquid, just can realize the photoresist material of this low amount to the effect of immersion liquid migration.
We have found that, acid and/or other photoresist material are problematic especially to undesirable migration in immersion liquid layer from photoresist layer.Acid or other photoresist material of moving in immersion liquid damage exposure tool and are reduced in the resolution that forms pattern in photoresist layer to I haven't seen you for ages.Therefore, photoresist of the present invention has formed important progress.
Be not bound by any theory, believe described and one or more photoresist resins substantially can not hybrid or multiple material migrate to the top area of applied photoresist coating, therefore suppressed photoresist material and outwards moved in the immersion liquid contacting with photoresist layer impregnated exposure step from photoresist layer.
In addition, by using multiple immiscible material, can control a plurality of offset printing character of photoetching compositions.For example, the top material of photoetching compositions can provide best water contact angle, thereby in dipping lithography processes, promotes the interaction with protective finish liquid.Described intermediate materials then can be used as main restraining mass, to avoid leaching.Use together two kinds of different materials (being top material and intermediate materials) also can provide to photoresist component adversely leaching enter the more effective control of protective finish immersion liquid.
In this article, with described one or more photoresist resins substantially immiscible material comprise after being added in photoresist and can cause photoresist material reduce migration or leach into these materials in immersion liquid.This type of material that substantially can not mix (non-mixable) can be by testing and easily determined according to experience with respect to contrast photoresist, and the composition of this contrast photoresist is identical from tested photoresist but different with the alternative material of immiscibility substantially.
Suitable immiscible material substantially for photoresist of the present invention comprises the component that comprises silicon and/or fluoro substituents.
For photoresist of the present invention preferably substantially immiscibility material can be particle form.This type of particle can comprise the polymkeric substance being polymerized with discrete particle form, as independent with separated polymer beads form.This type of polymer beads typically has one or more characteristics different from linearity or ladder polymer (as linear or trapezoidal silicon polymer).For example, this type of polymer beads can have size and the distribution of low molecular weight of regulation.More particularly, aspect preferred, photoresist of the present invention can be used many polymer beads, these particles have from approximately 5 dusts to 3000 dusts, be preferably approximately 5 dusts to 2000 dusts, better, from approximately 5 dusts to approximately 1000 dusts, better approximately 10 dusts are to approximately 500 dusts, the particle mean size (size) of best 10 dusts to 50 or 200 dusts.For many application, particularly preferred particle has the particle mean size lower than approximately 200 dusts or 100 dusts.
For photoresist of the present invention other preferably substantially immiscibility material can there is Si content, comprising silsesquioxane material, have SiO 2the material of group, etc.The preferred siliceous material of immiscibility substantially also comprises polyhedral oligomeric silsesquioxane.
Those that preferably contain photic acid-instability group (as photic acid-instability ester or acetal group, comprising the group using in the resin Composition of the photoresist strengthening at chemistry as herein described) are immiscibility material substantially.
Preferred immiscibility material substantially for photoresist of the present invention also will be dissolved in for preparing the identical organic solvent of this photoetching compositions.
The particularly preferred material of immiscibility substantially for photoresist of the present invention will have surface energy and/or the less fluid dynamics volume lower than one or more resins of photoresist resin Composition.Substantially immiscibility material isolation (segregation) or move to top or the top of applied photoresist coating described in lower surface can be able to promote.In addition, relatively little fluid dynamics volume is also preferred because it can promote one or more substantially immiscibility material effective mobility (higher coefficient of diffusion) in the top area of applied photoresist coating.
For photoresist of the present invention preferably substantially immiscible material also dissolve in photoresist developer composition (for example 0.26N aqueous alkali).Therefore, except photic acid-instability group as discussed above, described in other aqueous base-solubilizing group (as hydroxyl, fluorine alcohol, carboxyl etc.) also can be included in substantially in immiscible material.
The preferred imaging wavelength of lithographic system of the present invention comprises sub-400nm (as I-line (365nm)), sub-300nm wavelength (for example 248nm), and sub-200nm wavelength (for example 193nm).Except one or more are substantially immiscibility material, the particularly preferred photoresist of the present invention can contain photoactive component (for example one or more photic acid producing agent compounds) and one or more resins, and described resin is selected from:
1) phenolics that contains acid-instability group, it can provide the chemistry that is particularly suitable for imaging under 248nm to strengthen positive photoresist.The particularly preferred resin of this type comprises:
I) polymkeric substance that contains vinylphenol and alkyl acrylate polymerized unit can there is protective reaction in polymerized therein acrylic acid alkyl ester units under photic acid exists.The illustrative alkyl-acrylates that the protective reaction of photic acid induction can occur comprises, tert-butyl acrylate for example, Tert-butyl Methacrylate, acrylic acid methyl adamantane base ester, methyl methacrylate base adamantane esters, with the non-cycloalkanes ester of other acrylic acid that can experience photic acid-induced reaction and acrylate cyclic ester, as at United States Patent (USP) 6,042,997 and 5, polymkeric substance described in 492,793, these patents are incorporated herein by reference;
Ii) polymkeric substance that contains vinylphenol, the optional ethenylphenyl (for example styrene) (it is hydroxyl or carboxyl ring substituents not) replacing and alkyl acrylate (those as described in polymer i above remove blocking group) polymerized unit, as be described in United States Patent (USP) 6,042, polymkeric substance in 997, this patent is inserted herein by reference; With
Iii) contain the repetitive comprising the acetal with photic acid reaction or ketal structure division, and the polymkeric substance of optional aromatic repeating units (as phenyl or phenolic group); This base polymer has been described in United States Patent (USP) 5,929, and in 176 and 6,090,526, these patents are inserted herein by reference, and
I) and/or ii) and/or iii) blend;
2) do not contain the phenolics of acid-instability group, as poly-(vinylphenol) and novolac resin, they can be used from I-line and G-Lithography glue with two azo naphthoquinones Photoactive compounds one and be described in for example United States Patent (USP) 4,983,492; 5,130,410; 5,216,111; With 5,529, in 880;
3) substantially or completely not containing the resin of phenyl or other aromatic group, it can provide the chemistry being particularly suitable in the lower imaging of sub-200nm wavelength (as 193nm) to strengthen positive photoresist.The particularly preferred resin of this type comprises:
I) contain non-aromatic cycloolefin (endocyclic double bond) polymerized unit, as the polymkeric substance of the norborene of optional replacement, as be described in United States Patent (USP) 5,843, the polymkeric substance in 624 and 6,048,664, these patents are inserted herein by reference;
Ii) contain acrylic acid alkyl ester units, tert-butyl acrylate for example, Tert-butyl Methacrylate, acrylic acid methyl adamantane base ester, methyl methacrylate base adamantane esters, and the polymkeric substance of the non-alkane ester of other acrylic acid and acrylate cyclic ester; This base polymer has been described in United States Patent (USP) 6,057,083; The published application EP01008913A1 in Europe and EP00930542A1; In U.S. unexamined patent application 09/143,462, all these documents are inserted in this in full by reference, and
Iii) the acid anhydrides unit that contains polymerization, the polymkeric substance of the maleic anhydride of polymerization and/or itaconic anhydride unit particularly, as be disclosed in the published application EP01008913A1 in Europe and United States Patent (USP) 6,048, those in 662 (they are inserted in this in full by reference in full), and
I) and/or ii) and/or iii) blend;
4) contain heteroatoms, especially oxygen and/or sulphur, the resin of repetitive (but except acid anhydrides, this unit does not contain ketone annular atoms), and preferably this resin substantially or completely containing any aromatic units.Preferably, assorted alicyclic unit is fused on resin matrix, further preferably described resin comprises the alicyclic unit of the carbon condensing, and what for example for example, by polymerization norborene group and/or acid anhydrides unit (polymerization by maleic anhydride or itaconic anhydride forms), form condenses unit).This resinoid has been disclosed in PCT/US01/14914 and U.S. Patent application 09/567,634;
5) contain the substituent resin of Si-, comprise poly-(silsesquioxane) etc., and can use together with undercoat.This resinoid has for example been disclosed in United States Patent (USP) 6,803,171.
6) resin that contains fluoro substituents (fluoropolymer), for example, can fluoridize aromatic group as fluoro-distyryl compound by tetrafluoroethene, those resins that the compound that comprises hexafluoro alcohol structure division and analog polymerization form.This resinoid example has for example been disclosed in PCT/US99/21912.
Preferred photoresist of the present invention comprises positivity and the negative photoresist that chemistry strengthens simultaneously.The positive photoresist that typical preferred chemistry strengthens comprises one or more resins with photic acid-unstable group (as photic acid-instability ester or acetal group).
The present invention further provides the method for using photoresist of the present invention to form photoresist camegraph and produce electronic equipment.The present invention also provides the novel product that comprises the base material that scribbles photoetching compositions of the present invention.
Other side of the present invention is described hereinafter.
We find, add two or more different immiscible materials substantially can improve the offset printing performance of photoresist.
The good photoresist of the present invention comprises at least three kinds of different resins: the first resin that comprises photic acid labile group and the second and the 3rd different resins.Each in described resin better has different hydrophobicitys and surface energy, concrete as above-mentioned.Hydrophobicity and surface can be able to be measured by known method.For example, United States Patent (USP) 6927012 discloses the method for definite material surface energy.The hydrophobicity of material can be determined by high speed liquid chromatography method.The molecular weight of each in described the first resin that comprises photic acid labile group and different the second and the 3rd resin can be in wide scope, for example Mw is about 1000-100000, Mw is more generally 1500-8000,10000,15000,20000,30000,40000 or 50000, and polydispersity is about 4,3,2 or lower.
With reference to Fig. 1, it has described schematically photoetching compositions 10 preferably, and this photoetching compositions 10 has been spin-coated on silicon wafer 12.The photoetching compositions layer applying has carried out soft baking (soft-baked) (for example 105 ℃, continue 60 seconds), to remove desolventizing.As shown in Figure 1, the material of photoresist is separable into different regions, be that one or more resins with photic acid labile group are located substantially in region 14, described region 14 approaches the surface of described base material 12 most, then be intermediate materials (trimer for example with hexafluoro alcohol (hexafluoroalcohol) and carboxyl), in its zone line 16 shown in being located substantially on, then be top polymkeric substance (for example polar group is less than the multipolymer of described intermediate materials), it substantially based on shown in top area 18 in.
As discussed above, with described photoresist resin Composition substantially the suitable material of immiscible photoresist of the present invention can easily determine by simple experiment.Specifically, as mentioned here, process with according to same way but do not contain the same photoresist system of immiscibility material substantially and compare, the photoetching compositions that contains immiscibility material by use, preferred immiscibility material substantially will reduce the amount of in immersion liquid detectable acid or organic material.In immersion liquid, the detection of photoresist material can be carried out according to method described in the embodiment 2 below, comprises this immersion liquid mass spectrophotometry before contact lithograph glue and afterwards.In this alanysis, in exposure process, make the direct and tested photoetching compositions of this immersion liquid contact and reach approximately 60 seconds.Preferably, with do not use the same photoresist of immiscibility material substantially and compare, add one or more substantially immiscibility material can make photoresist material residual in immersion liquid (same, the acid being detected by mass spectrometer or organism) amount be reduced by least 10%, more preferably, with do not contain described in substantially the same photoresist of immiscibility material compare, described one or more substantially immiscibility material can make photoresist material residual in immersion liquid (same, acid or organism) amount be reduced by least 20%, 50%, or 100%, 200%, 500%, or 1000%.
As above-mentioned, concrete preferred immiscibility material substantially comprises the material containing Si.The especially preferred material of immiscibility substantially comprises nano-structured composition, they can be from such as mixed plastic (Hybrid Plastics) (Valley, the court of a feudal ruler, California, USA side) (Fountain Valley, California), the company of Sigma/Alder Ritchie (Sigma/Aldrich) etc. and so on is purchased.This type of material can comprise: the molecular oxygen SiClx with the Si-O core being surrounded by organic group; Silanol; And polymkeric substance and resene, they comprise the compound of silsesquioxane cage structure and can be siloxane, styrene resin, and acrylic resin, the alicyclic ring same clan is as norbornene resin and other analog.
Being used as the particle of immiscibility material (comprising organic granular) substantially comprises containing Si and material that fluoridize.This type of particle is commercially available, or can easily synthesize, for example, by one or more monomers, react together with (if necessary) initiator compounds with crosslinking chemical.The monomer reacting can have substituting group as need, fluorine for example, Si group, photic acid-instability group (as photic acid-instability ester or acetal), other alkali-solubilization radical (as alcohol) etc.For the illustrative of this type of particle of producing by multiple different monomers is synthetic can be referring to embodiment 1 below, a kind of in these monomers provides photic acid-instability group for resulting polymers particle.
This substantially immiscibility material be present in photoetching compositions and effective result is still provided with lower amount.For example, described one or more substantially immiscibility material be applicable to existing with the amount of the approximately 0.1-20wt% of the general assembly (TW) based on flow-like photoetching compositions.Suitable amount also provides in embodiment below.
As mentioned above; be applicable to the photoresist that preferred photoresist of the present invention comprises the chemistry enhancing of positivity or negativity; i.e. a kind of like this negative photoresist composition; there is the cross-linking reaction of photic acid-promotion and make the developer solubility of photoresist coating exposure region lower than unexposed area in it; or a kind of like this positive photoresist composition; there is the protective reaction of photic acid-promotion of the acid labile group of one or more composition component in it, makes the solubleness of water developer of photoresist coating exposure region higher than the water developer solubleness of unexposed area.Contain with covalent bond and be connected to non-annularity tertiary alkyl carbon (for example tert-butyl group) on ester group carboxyl oxygen or the ester group of alicyclic tertiary carbon (for example methyl adamantane base) is usually the preferred photic acid-instability group for photoresist resin of the present invention.Photic acid-the instability of acetal group is also preferred.
Preferred photoresist of the present invention typically comprises resin Composition and photoactive component.Preferably, this resin has and makes photoetching compositions have the functional group that aqueous alkali can developability.For example, the resinoid bond that preferably comprises polar functional group (as hydroxyl or carboxylate).Preferably, in photoetching compositions, the consumption of resin Composition enough makes photoresist be developed by aqueous alkali solution.
For the imaging being greater than under the wavelength of 200nm (as 248nm), phenolics typical case is preferred.Preferred phenolics is poly-(vinylphenol), and it can form by block copolymerization, emulsion polymerization or the solution polymerization under catalyzer exists by corresponding monomer.Vinylphenol for the manufacture of polyvinyl phenol resin can for example make as follows: cumarin or substituted cumarin that hydrolysis is purchased, make the decarboxylation of gained hydroxycinnamic acid subsequently.Useful vinylphenol also can or be prepared by the decarboxylation of hydroxycinnamic acid by the dehydration of corresponding hydroxy alkyl phenols, and described hydroxycinnamic acid is by replacing or unsubstituted hydroxy benzaldehyde forms with reacting of malonic acid.The preferred polyvinylphenol resin of preparing from this type of vinylphenol class has approximately 2,000 to approximately 60,000 daltonian molecular weight.
More fortunately be greater than the photoresist that under the wavelength of 200nm (as 248nm), imaging also has chemistry to strengthen, it comprises photoactive component and the resin Composition of blending, and described resin Composition comprises the multipolymer that contains phenol type and non-phenol type unit.For example, one group of good this analog copolymer has acid labile group, this acid-unstable group substantially, mainly or fully only on the non-phenol type unit of multipolymer, the especially photic acid-instability of alkyl acrylate group, i.e. phenol-alkyl acrylate copolymer.A kind of especially preferred copolymer binder has repetitive x and the y of following general formula:
Wherein this hydroxyl can be present in the neighbour of multipolymer, or contraposition on, and R ' has approximately 18 carbon atoms of 1-, more typically replacement or the unsubstituted alkyl of approximately 6 to 8 carbon atoms of 1-.The tert-butyl group is general preferred R ' group.R ' group can be optionally by for example one or more halogens (special F, Cl or Br), C 1-8alkoxy, C 2-8alkenyl, etc. replace.Unit x and y can be in multipolymer alternately exist regularly, or can random distribution in whole polymkeric substance.This analog copolymer can easily form.For example, for the resin of above general formula, vinyl phenols and replacement or unsubstituted alkyl acrylate (as tert-butyl acrylate etc.) can condition of free radical known in the prior art under condensation.The replacement ester structure part of acrylic ester unit, R '-O-C (=O)-structure division, is used as the acid labile group of resin and after the photoresist coating exposure that contains this resin, photic sour induced fission occurs.Preferably the Mw of this multipolymer is from approximately 8,000 to approximately 50,000, and more preferably from about 15,000 to approximately 30,000, have approximately 3 or lower molecular weight distribution, more preferably from about 2 or lower molecular weight distribution.Non-phenol resin, for example the multipolymer of alkyl acrylate (as tert-butyl acrylate or Tert-butyl Methacrylate) and vinyl alicyclic ring family hydrocarbon (as vinyl norbornene alkyl or vinyl cyclohexanol compounds), also can be used as the resinoid bond in the present composition.This analog copolymer also can be prepared by free radical polymerization or other known method, and suitablely has approximately 8,000 to approximately 50,000 Mw, and approximately 3 or lower molecular weight distribution.
The photoresist strengthening for positivity of the present invention chemistry have acid-instability go other preferred resin of blocking group have been disclosed in the european patent application 0829766A2 (resin with acetal and ketal group) of Sipray Co (Shipley Company) and the European patent application EP 0783136A2 of Sipray Co (Shipley Company) (terpolymer and other multipolymer, they comprise the unit of following monomer: 1) styrene; 2) hydroxy styrenes; With 3) acid labile group, particularly alkyl acrylate acid labile group (as tert-butyl acrylate or Tert-butyl Methacrylate).Conventionally, the resin with various acid labile groups will be suitable, as the ester of acid labile, and carbonic ester, ether, acid imide, etc.The common side joint of this photic acid labile group is on polymer backbone, although also can use the resin with the acid labile group being incorporated on polymer backbone.
As discussed above, for the imaging at Asia-200nm (as 193nm) wavelength, preferably use a kind of like this photoresist, it contains one or more and substantially, mainly or does not fully contain the polymkeric substance of phenyl or other aromatic group.For example, for Asia-200nm imaging, preferred photoresist polymkeric substance contains lower than about 5mol% aromatic group, more preferably less than approximately 1 or 2mol% aromatic group, more preferably less than about 0.l, 0.02,0.04 and 0.08mol% aromatic group and again more preferably less than about 0.01mol% aromatic group.Particularly preferred polymkeric substance is not fully containing aromatic group.Aromatic group can high absorption Asia-200nm radiation, for the polymkeric substance using in the photoresist with this type of short wavelength radiation imaging, be therefore undesirable.
Substantially or fully containing suitable polymer aromatic group and that available PAG of the present invention prepares to obtain for the photoresist of Asia-200nm imaging, do not have been disclosed in European application EP930542A1 and United States Patent (USP) 6,692,888 and 6,680,159, all belong to Sipray Co (Shipley Company).
Substantially or completely containing the suitable acrylic ester unit that contains of suitable polymer of aromatic group, (for example can not pass through acrylic acid methyl adamantane base ester, methyl methacrylate base adamantane esters, acrylic acid ethyl fenchyl ester, photic acid-instability acrylic ester unit that the polyreaction of methacrylic acid ethyl fenchyl ester and analog provides); The non-aromatic alicyclic group condensing (for example can provide by norbornene compound or the polyreaction with other alicyclic compound of interior ring carbon-to-carbon double bond); And acid anhydrides (for example can providing by the polyreaction of maleic anhydride and/or itaconic anhydride); Etc..
Preferred negativity compound of the present invention is included in one or more materials (as crosslinking chemical component, for example amine-sill is as melamine resin) that curing, crosslinked or sclerosis occur while touching acid, and photoactive component of the present invention.Particularly preferred negativity composition comprises resinoid bond, as phenolics, and crosslinking chemical component and photoactive component of the present invention.Such composition and its use have been disclosed in european patent application 0164248 and 0232972 and in the people's such as Thackeray U.S. Patent No. 5,128,232.As the preferred phenolics of resinoid bond component, comprise novolac, and poly-(vinyl phenols), as discussed above those.Preferred crosslinking chemical comprises amine-sill, comprising melamine, and glycoluril, benzo melamine-sill and urea-sill.Melamine-formaldehyde resin is generally most preferred.This type of crosslinking chemical is commercially available, for example the melamine resins with trade name Shamir (Cymel) 300,301 and 303 sales by American Cyanamid Company (American Cyanamid).Glycoluril resin Shi You American Cyanamid Company (AmericanCyanamid) is with trade name Shamir (Cymel) 1170,1171,1172 sales, urea-Ji resin is with trade name bit (Beetle) 60,65 and 80 sales, benzo melamine resin is sold with trade name Shamir (Cymel) 1123 and 1125.
For imaging under Asia-200nm wavelength (as 193nm), preferred negative photoresist has been disclosed in the WO 03077029 of Sipray Co (Shipley Company).
Photoresist of the present invention also can contain other material.For example, other optional adjuvant comprises photochemical and contrast dyestuff, anti-striped reagent, plastifier, speed reinforcing agent, sensitizer (for example, for using the photic acid producing agent of the present invention at longer wavelength under as I-line (being 365nm) or G-line wavelength), etc.The adjuvant of examples of such optional is typically present in photoetching compositions with low concentration, but except filler and dyestuff, they can exist with larger concentration, for example, in the amount of the 5-30wt% of the general assembly (TW) of the dry component of photoresist.
The preferred optional additives of photoresist of the present invention is the alkali adding, caprolactam for example, and it can strengthen the resolution of the photoresist camegraph having developed.The alkali that adds is suitable to be used with small amount, for example, with respect to the approximately 1-10wt% of photic acid producing agent, and the about 5wt% of more typical 1-.Other suitable alkalinity additive comprises sulfonic acid ammonium salt, as p-toluenesulfonic acid piperidines and p-toluenesulfonic acid dicyclohexyl ammonium; Alkyl amine is as tripropyl amine (TPA) and lauryl amine; Aryl amine is as diphenylamine, triphenyl amine, amino-phenol, and 2-(4-aminophenyl)-2-(4-hydroxyphenyl) propane.
The resin Composition of photoresist of the present invention is typically enough to make the coating of photoresist exposure be used by the amount that for example aqueous alkali develops.More particularly, resin binder is by the about 90wt% of the 50-that accounts for aptly photoresist total solid.This photoactive component should exist enough to produce the amount of sub-image in the coating of photoresist.More particularly, the amount of the suitable approximately 1-40wt% with photoresist total solid of this photoactive component exists.Typically, the photoresist that the photoactive component of small amount strengthens for chemistry is suitable.
Photoetching compositions of the present invention also comprises photic acid producing agent (i.e. " PAG "), and it is suitable to enough to produce the amount use of sub-image in the coating of photoresist after being exposed to actinic radiation.For preferred PAG imaging under 193nm and 248nm, comprise imide sulphonic acid ester, as shown in the formula compound:
Figure G2008101761432D00121
Wherein R is camphanone, diamantane, alkyl (C for example 1-12alkyl) and perfluoroalkyl, as perfluor (C 1-12alkyl), Perfluorooctane sulfonates root especially, Perfluorononane sulfonate radical etc.Particularly preferred PAG is N-[(PFO sulfonyl) oxygen base]-5-norborene-2,3-dicarboximide.
Sulfonate compound is also suitable PAG, special sulfonate.Two kinds of suitable agent that 193nm and 248nm imaging are used are following PAG 1 and 2:
This type of sulfonate compound can be according to disclosed method preparation in european patent application 96118111.2 (publication No. 0783136), and it describes the synthetic of above PAG 1 in detail.
Also suitable is the above two kinds of iodine compounds that coordinate with above-mentioned camphorsulfonic acid root other negative ion in addition.Especially, preferably negative ion comprises general formula R SO 3-those, wherein R is diamantane, alkyl (C for example 1-12alkyl) and perfluoroalkyl as perfluor (C 1-12alkyl), Perfluorooctane sulfonates root especially, perfluorinated butane sulfonate radical etc.
Other known PAG can be used in photoresist of the present invention.For 193nm imaging, the general PAG that does not preferably contain aromatic group, as above-mentioned imide sulphonic acid ester, to the transparency of enhancing is provided especially.
Photoresist of the present invention also can contain other optional material.For example, other optional adjuvant comprises anti-striped reagent, plastifier, and speed reinforcing agent, etc.The adjuvant of examples of such optional is typically present in photoetching compositions with low concentration, but except filler and dyestuff, they can exist with relatively large concentration, for example, with the amount of the approximately 5-30wt% of the general assembly (TW) of photoresist dried ingredients.
The photoresist that the present invention uses is generally prepared in accordance with known methods.For example, photoresist of the present invention can be by the components dissolved of photoresist is made as coating composition in suitable solvent, and for example, glycol ethers is as 2-methoxy ethyl ether (diethylene glycol dimethyl ether), glycol monoethyl ether, propylene glycol monomethyl ether for this solvent; Propylene glycol methyl ether acetate; Lactate is as ethyl lactate or methyl lactate, and wherein ethyl lactate is preferred; Propionic ester, methyl propionate especially, ethyl propionate and ethoxy-propionic acid ethyl ester, cellosolve ester is as methylcellosolve acetate; Aromatic hydrocarbons is as toluene or dimethylbenzene; Or ketone is as MEK, cyclohexanone and 2-HEPTANONE.Typically, the solids content of photoresist changes accounting between the 5wt% of photoetching compositions general assembly (TW) and 35wt%.The blend of this kind solvent is also suitable.
Liquid photoresist composition can be by for example spin-coating method, dip coating, and roll coating process or other common coating technique are applied on base material.When spin coating, can be according to used concrete spin-coating equipment, the viscosity of solution, the solids content of the time span adjusting coating solution that the speed of spinner and spin coating are used, to obtain required film thickness.
Suitable being applied on the base material of conventionally processing with photoresist (comprising coating) of photoetching compositions that the present invention uses.For example, described composition can be applied on silicon wafer or be applied on the silicon wafer that scribbles silicon dioxide, to produce microprocessor and other integrated circuit component.Also suitable use aluminium-aluminium oxide, gallium arsenide, pottery, quartz, copper, glass baseplate etc.Photoresist is suitable being applied on anti-reflecting layer also, especially on organic antireflection layer.
After on photoresist paint surface, it can be by heat drying to remove desolventizing, until preferably this photoresist coating is inviscid.
Described photoresist layer (the barrier compositions layer that has cover to be coated with subsequently exposes in immersion lithography art system, if present), at exposure tool (especially projecting lens) with apply space between the base material of photoresist and occupied by immersion liquid (if water or water and one or more adjuvants are as the potpourri of cesium sulfate (it can make fluid have the refractive index of enhancing)).Preferably, this immersion liquid (for example, water) is treated to avoid bubble, for example, can carry out water degassed to avoid nano-scale bubble.
Term " impregnated exposure " or other similar terms refer to herein, and exposure is for example, to carry out with being placed in fluid layer between the photoetching compositions layer of exposure tool and coating (water or have the water of adjuvant).
This photoetching compositions layer is then suitable uses typical case at about 1-100mJ/cm 2exposure energy in scope is exposed to activating radiation in pattern mode, and this depends on the component of exposure tool and photoetching compositions.Term " is exposed to photoetching compositions the radiation that can activate this photoresist " and refers to herein, and radiation can form sub-image in photoresist, as for example, by causing the reaction (producing photic acid from photic acid producing agent compound) of photoactive component.
As discussed above, photoetching compositions preferably carrys out photoactivation by short exposure wavelength, sub-400nm especially, sub-300 and sub-200nm exposure wavelength, I-line (365nm) wherein, 248nm and 193nm and EUV and 157nm are particularly preferred exposure wavelengths.
After exposure, the rete of composition preferably toasts at the temperature within the scope of approximately 70 ℃ to approximately 160 ℃.Thereafter, film is developed, this preferably passes through use alkali developer as quaternary phosphonium hydroxides ammonium salt solution (as tetraalkylammonium hydroxide solution); Various amine aqueous solutions (preferably 0.26N tetramethyl ammonium hydroxide), as ethamine, n-pro-pyl amine, diethylamide, di-n-propyl amine, triethylamine, or methyl diethylamide; Hydramine is as diethanolamine or triethanolamine; Cyclammonium class is as pyrroles, and pyridine etc. is processed and implemented.Conventionally, develop and carry out according to program commonly known in the art.
After the development of the photoresist coating on base material, the base material developing can be processed selectively on those regions exposed from photoresist, for example, according to program well known in the prior art, by with chemical mode etching or plating exposed substrate regions from photoresist.For the manufacture of microelectronic substrates, for example, the manufacture of silica wafers, suitable etchant comprises gaseous etchant, for example halogen plasma etchant is as chloro or fluoro-base etchant, as with the streamed Cl applying of plasma 2or CF 4/ CHF 3etchant.After this type of processing, photoresist can be by being used known stripping means to remove from the base material of processing.
All documents mentioned in this article are inserted in this by reference in full.Following non-limiting examples is used for illustrating the present invention.
embodiment 1: particulate additive preparation
Preferably fluoridizing particulate additive is prepared as follows:
In reaction vessel, pack the propylene glycol methyl ether acetate (PGMEA) of aequum into and be heated to 80 ℃, using N 2gas purging.By following monomer (PFPA, ECPMA, TMPTA), crosslinking chemical and initiating agent (crossing neopentanoic acid tertiary pentyl ester) are blended in PGMEA to account for the amount of fluid composition 80-90wt% in ice bath.This initiator content is with respect to 4% of monomer and crosslinking chemical total amount.The following row weight consumption of monomer is used: 70wt% five fluorinated monomers (PFPA), and 20wt% methacrylic acid ethyl cyclopentyl ester (ECPMA), and 10wt%TMPTA:
Figure G2008101761432D00141
This monomer/crosslinking chemical/initiating agent/PGMEA potpourri then with approximately 1 person of outstanding talent raw/minute speed join in reactor.After process in joining reactor finishes, the temperature of the potpourri in reactor keeps 30 minutes at 80 ℃.Then, the initiating agent of other 2wt% (with respect to monomer and crosslinking chemical total amount) is joined in reactor.After adding, the temperature of the potpourri in reactor keeps other 2 hours at 80 ℃.Thereafter, the temperature of reactor is cooled to room temperature.
By this program, obtained polymer beads, it has 7088 number-average molecular weight (Mn) and 19255 weight-average molecular weight (Mw).
embodiment 2: photoresist preparation and fabrication
By the following material of amount blending in accordance with regulations, prepare photoetching compositions:
1. resin Composition: the terpolymer of (methacrylic acid 2-methyl-2-adamantane esters/beta-hydroxy-gamma-butyrolactone methacrylate/cyano group-norborny methacrylate), consumption is the 6.79wt% of photoetching compositions general assembly (TW);
2. photic acid producing agent compound: tert-butyl-phenyl tetramethylene sulfonium perfluorinated butane sulfonate, consumption is the 0.284wt% of photoetching compositions general assembly (TW);
3. alkali adjuvant: N-alkyl caprolactam, consumption is the 0.017wt% of photoetching compositions general assembly (TW);
4. surfactant: R08 (fluorine-containing surfactant can obtain from Mount Tai Japanese ink and chemical company (Dainippon Ink & Chemicals, Inc.)), consumption is the 0.0071wt% of photoetching compositions general assembly (TW);
5. immiscible adjuvant substantially:
(i) top resin material: content is the multipolymer of following two kinds of monomers of 50 % by mole, and its structure is as follows: 2-(4,4,4-couple-trifluoromethyl hydroxyl) butyl methyl acrylate: tert-butyl group methacrylate
Figure G2008101761432D00151
(ii) intermediate materials: 88/8/4 terpolymer of following structure (in following structure, from left to right the mole percentage of corresponding monomer is 88/8/4):
Figure G2008101761432D00161
6. solvent composition: propylene glycol methyl ether acetate, provides approximately 90% fluid composition.
Above-mentioned photoetching compositions is spun onto on silicon wafer, dry to remove film (soft-plate) on heating in vacuum plate, then adopt immersion lithography technique to make the direct contact drying photoresist layer of water-based immersion liquid, dry photoresist film is implemented to exposure.In this dipping systems, photoresist layer is the patterning 193nm radiation of 24.1 milli Jiao/square centimeters in dosage by photomask exposure.
Then this photoresist layer carries out postexposure bake (as at about 120 ℃), with 0.26N alkali reagent solution, develops, and obtains photoresist camegraph.
For the leaching of evaluating photoresist component after post exposure bake and before developing, by photic acid and light degradation accessory substance thereof in the photoresist of LC/ mass spectrum (60 seconds leaching time tests) evaluation steeping liq.
embodiment 3: other photoresist preparation and fabrication
By the following material of amount blending in accordance with regulations, prepare another kind of photoetching compositions:
1. resin Composition: the terpolymer of (methacrylic acid 2-methyl-2-adamantane esters/beta-hydroxy-gamma-butyrolactone methacrylate/cyano group-norborny methacrylate), consumption is the 6.79wt% of photoetching compositions general assembly (TW);
2. photic acid producing agent compound: tert-butyl-phenyl tetramethylene sulfonium perfluorinated butane sulfonate, consumption is the 0.284wt% of photoetching compositions general assembly (TW);
3. alkali adjuvant: N-alkyl caprolactam, consumption is the 0.017wt% of photoetching compositions general assembly (TW);
4. surfactant: R08 (fluorine-containing surfactant can obtain from Mount Tai Japanese ink and chemical company (Dainippon Ink & Chemicals, Inc.)), consumption is the 0.0071wt% of photoetching compositions general assembly (TW);
5. immiscible adjuvant substantially, its consumption is 0.213 % by weight of described photoetching compositions general assembly (TW).Described immiscible component substantially comprises following two kinds of different top material and intermediate materials:
(i) top resin material: content is the multipolymer of following two kinds of unit of 50 % by mole, and its structure is as follows:
Figure G2008101761432D00171
(ii) intermediate materials: 25/25/20/30 terpolymer of following structure (in following structure, from left to right the mole percentage of corresponding monomer is 25/25/20/30):
6. solvent composition: propylene glycol methyl ether acetate, provides approximately 90% fluid composition.
As described in above-described embodiment 2, identical method is processed this photoetching compositions.
embodiment 4: other photoresist preparation and fabrication
By the following material of amount blending in accordance with regulations, prepare another kind of photoetching compositions:
1. resin Composition: the terpolymer of (methacrylic acid 2-methyl-2-adamantane esters/beta-hydroxy-gamma-butyrolactone methacrylate/cyano group-norborny methacrylate), consumption is the 6.79wt% of photoetching compositions general assembly (TW);
2. photic acid producing agent compound: tert-butyl-phenyl tetramethylene sulfonium perfluorinated butane sulfonate, consumption is the 0.284wt% of photoetching compositions general assembly (TW);
3. alkali adjuvant: N-alkyl caprolactam, consumption is the 0.017wt% of photoetching compositions general assembly (TW);
4. surfactant: R08 (fluorine-containing surfactant can obtain from Mount Tai Japanese ink and chemical company (Dainippon Ink & Chemicals, Inc.)), consumption is the 0.0071wt% of photoetching compositions general assembly (TW);
5. immiscible adjuvant substantially, its consumption is 0.213 % by weight of described photoetching compositions general assembly (TW).Described immiscible component substantially comprises following two kinds of different top material and intermediate materials:
(i) top resin material: 70/30 multipolymer of following structure (in following structure, from left to right the mole percentage of corresponding units is 70/30):
Figure G2008101761432D00181
(ii) intermediate materials: 25/25/20/30 terpolymer of following structure (in following structure, from left to right the mole percentage of corresponding units is 25/25/20/30):
Figure G2008101761432D00182
6. solvent composition: 50/50 (volume ratio) ethyl lactate: propylene glycol methyl ether acetate blend, provides approximately 90% fluid composition.
As described in above-described embodiment 2, identical method is processed this photoetching compositions.
Foregoing description of the present invention is only exemplary, is appreciated that its changes and improvements do not leave scope or the spirit of following claims of the present invention.

Claims (8)

1. process a method for photoetching compositions, described method comprises:
(a) on base material, apply photoetching compositions, described photoetching compositions comprises:
(i) one or more resins;
(ii) photoactive component; And
Two kinds substantially can not with the material of described one or more mixed with resin, described two kinds can not comprise (1) top material and (2) intermediate materials with the material of described one or more mixed with resin substantially, the described photoetching compositions applying has formed one deck photoresist layer, the major part that the major part of wherein said one or more resins is compared described intermediate materials more approaches described base material, the major part of described intermediate materials is compared described top material and is more approached described base material, and described top material is compared intermediate materials and had larger hydrophobicity; With
(b) described photoresist layer dipping is exposed to irradiation, to activate described photoetching compositions,
Described top material is selected from following material:
Respectively the do for oneself multipolymer of following two kinds of monomers of 50 % by mole of content
Figure FDA0000399656530000011
Respectively the do for oneself multipolymer of following two kinds of unit of 50 % by mole of content, its structure is as follows:
Figure FDA0000399656530000012
70/30 multipolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding units is 70/30:
Figure FDA0000399656530000021
Described intermediate materials is selected from following material:
88/8/4 terpolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding monomer is 88/8/4:
Figure FDA0000399656530000022
25/25/20/30 quadripolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding monomer is 25/25/20/30:
Figure FDA0000399656530000023
25/25/20/30 quadripolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding units is 25/25/20/30:
Figure FDA0000399656530000031
2. the method for claim 1, is characterized in that, described top and intermediate materials have different surface energy.
3. the method as described in any one in claim 1-2, is characterized in that, the hydrophobicity of described top material and intermediate materials is greater than the hydrophobicity of described one or more resins.
4. the method as described in any one in claim 1-2, it is characterized in that described two kinds can not comprise resin with the material of described one or more mixed with resin substantially, described resin comprises aqueous base-solubilizing group and/or one or more photic acid labile group and/or silicon or fluoro substituents.
5. a base material system for coating, described system comprises:
The base material on it with photoetching compositions coating, described photoetching compositions comprises:
(i) one or more resins;
(ii) photoactive component; And
Two kinds substantially can not with the material of described one or more mixed with resin, described two kinds can not comprise (1) top material and (2) intermediate materials with the material of described one or more mixed with resin substantially, in described photoetching compositions coating, the major part that the major part of described one or more resins is compared described intermediate materials more approaches described base material, the major part of described intermediate materials is compared described top material and is more approached described base material, described top material is compared intermediate materials and is had larger hydrophobicity
Described top material is selected from following material:
Respectively the do for oneself multipolymer of following two kinds of monomers of 50 % by mole of content
Respectively the do for oneself multipolymer of following two kinds of unit of 50 % by mole of content, its structure is as follows:
Figure FDA0000399656530000042
70/30 multipolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding units is 70/30:
Figure FDA0000399656530000043
Described intermediate materials is selected from following material:
88/8/4 terpolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding monomer is 88/8/4:
Figure FDA0000399656530000044
25/25/20/30 quadripolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding monomer is 25/25/20/30:
25/25/20/30 quadripolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding units is 25/25/20/30:
Figure FDA0000399656530000052
6. system as claimed in claim 5, is characterized in that immersion lithography liquid contacts the top surface of described photoetching compositions coating.
7. system as claimed in claim 5, is characterized in that described system also comprises immersion lithography exposure tool.
8. a photoetching compositions, described photoetching compositions comprises:
(i) one or more resins;
(ii) photoactive component; And
Two kinds substantially can not with the material of described one or more mixed with resin, described two kinds can not comprise (1) top material and (2) intermediate materials with the material of described one or more mixed with resin substantially, described photoetching compositions has formed one deck on base material, the major part that the major part of wherein said one or more resins is compared described intermediate materials more approaches described base material, the major part of described intermediate materials is compared described top material and is more approached described base material, described top material is compared intermediate materials and is had larger hydrophobicity
Described top material is selected from following material:
Respectively the do for oneself multipolymer of following two kinds of monomers of 50 % by mole of content
Respectively the do for oneself multipolymer of following two kinds of unit of 50 % by mole of content, its structure is as follows:
Figure FDA0000399656530000062
70/30 multipolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding units is 70/30:
Figure FDA0000399656530000063
Described intermediate materials is selected from following material:
88/8/4 terpolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding monomer is 88/8/4:
Figure FDA0000399656530000064
25/25/20/30 quadripolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding monomer is 25/25/20/30:
Figure FDA0000399656530000071
25/25/20/30 quadripolymer of following structure, in following structure, from left to right the ratio of the mole percentage of corresponding units is 25/25/20/30:
Figure FDA0000399656530000072
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